KR20130007162A - Novel heterocyclic compound and organic light emitting device containing same - Google Patents

Novel heterocyclic compound and organic light emitting device containing same Download PDF

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KR20130007162A
KR20130007162A KR1020110064077A KR20110064077A KR20130007162A KR 20130007162 A KR20130007162 A KR 20130007162A KR 1020110064077 A KR1020110064077 A KR 1020110064077A KR 20110064077 A KR20110064077 A KR 20110064077A KR 20130007162 A KR20130007162 A KR 20130007162A
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임진오
황석환
김영국
정혜진
한상현
이보라
이종혁
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삼성디스플레이 주식회사
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    • C07D221/02Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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    • Y10S428/00Stock material or miscellaneous articles
    • Y10S428/917Electroluminescent

Abstract

The present invention relates to an organic light emitting device having a heterocyclic compound represented by Chemical Formula 1 and an organic film including the same:
≪ Formula 1 >
Figure pat00054

For the description of the above formula, see the detailed description of the invention.

Description

Novel heterocyclic compound and organic light emitting device containing same

It relates to a heterocyclic compound represented by Formula 1 and an organic light emitting device including the same.

Electroluminescent devices are attracting attention because they have a wide viewing angle, excellent contrast, and fast response time. The organic electroluminescent device is classified into an inorganic electroluminescent device using an inorganic compound as an emitting layer and an organic EL device using an organic compound. Among these, the organic EL device has a higher luminance than an inorganic electroluminescent device. In particular, many studies have been conducted in that driving voltage and response speed are excellent and multicoloring is possible. The organic electroluminescent device generally has a stacked structure of an anode / organic light emitting layer / cathode, and further includes a hole injection layer and / or a hole transport layer and an electron injection layer between the anode and the light emitting layer or between the light emitting layer and the cathode to form an anode / hole transport layer. / Organic light emitting layer / cathode structure, anode / hole transport layer / organic light emitting layer / electron transport layer / cathode and the like.

As such an organic light emitting layer material, for example, an anthracene derivative and the like are known, but the organic light emitting device including the organic light emitting material known so far does not reach a satisfactory level of life, efficiency, and power consumption characteristics, and there is a lot of room for improvement.

One aspect of the present invention is to provide a novel heterocyclic compound having improved electrical properties, charge transport ability and luminescent ability.

Another aspect of the present invention to provide an organic light emitting device comprising the heterocyclic compound.

Another aspect of the present invention is to provide a flat panel display device having the organic light emitting device.

According to one aspect of the present invention, a heterocyclic compound represented by Formula 1 is provided:

≪ Formula 1 >

Figure pat00001

In Formula 1, R 1 to R 13 are each independently a hydrogen atom, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, and having 2 to 60 carbon atoms. A substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, 5 carbon atoms An amino group substituted with a substituted or unsubstituted arylthio group having from 60 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, an aryl group having 5 to 60 carbon atoms or a heteroaryl group having 3 to 60 carbon atoms, and having 3 to 60 carbon atoms Substituted or unsubstituted heteroaryl group, substituted or unsubstituted condensed polycyclic group having 6 to 60 carbon atoms, halogen atom, cyano group, nitro group, hydroxy group or carboxy group, R 1 and R 2 are May be combined with each other to form an aromatic ring.

According to an embodiment of the present invention, in Formula 1, R 1 , R 2 and R 8 are each independently a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, substituted or unsubstituted C 3 to 20 carbon atoms It may be a heteroaryl group, or a substituted or unsubstituted condensed polycyclic group having 5 to 20 carbon atoms.

According to an embodiment of the present invention, in Formula 1, R 3 to R 7 and R 9 to R 13 may be each independently hydrogen or deuterium.

According to another embodiment of the present invention, in Formula 1, R 1 and R 2 are each independently hydrogen, deuterium, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, or any one of the following Formulas 2a to 2e: Can be:

Figure pat00002

In Formulas 2a to 2e, Q 1 is a linking group represented by -C (R 14 ) (R 15 )-, -N (R 16 )-, -S- or -O-; Y 1 , Y 2 and Y 3 are independently of each other a linking group represented by -N =, -N (R 17 )-or -C (R 18 ) =; Z 1 , Z 2 , R 14 , R 15 , R 16 , R 17 and R 18 are each independently a hydrogen atom, deuterium, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, A substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted condensed polycyclic group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group or a carboxy group; p is an integer from 1 to 12; * Represents a bond.

According to another embodiment of the present invention, in Formula 1, R 8 may be any one of the following Formulas 3a to 3j:

Figure pat00003

In Formulas 3a to 3j, Q 1 is a linking group represented by -C (R 14 ) (R 15 )-, -N (R 16 )-, -S-, or -O-; Y 1 , Y 2 and Y 3 are independently of each other a linking group represented by —O—, —N =, —N (R 17 ) — or —C (R 18 ) =; Z 1 , Z 2 , Ar 12 , Ar 13 , R 14 , R 15 , R 16 , R 17 And R 18 independently of each other, a hydrogen atom, deuterium, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, and having 6 to 6 carbon atoms 20 substituted or unsubstituted condensed polycyclic group, halogen atom, cyano group, nitro group, hydroxy group or carboxy group; Ar 11 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 5 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms; p is an integer from 1 to 12; r is an integer from 0 to 5; * Represents a bond.

According to another embodiment of the present invention, in Formula 1, R 1 and R 2 are each independently hydrogen, deuterium, or any one of the following Formulas 4a to 4g, or may be bonded to each other to form a benzene ring. have:

Figure pat00004

In Formulas 4a to 4g, Z 1 and Z 2 independently of each other, a hydrogen atom, deuterium, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, a substituted or unsubstituted carbon atom 3 to 20 A substituted heteroaryl group, a substituted or unsubstituted condensed polycyclic group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group or a carboxy group; p is an integer from 1 to 6; * Represents a bond.

According to another embodiment of the present invention, in Formula 1, R 8 may be any one of the following Formulas 5a to 5o:

Figure pat00005

In Formulas 5a to 5o, Z 1 , Z 2 , Ar 12, and Ar 13 are each independently a hydrogen atom, deuterium, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, and 3 carbon atoms. A substituted or unsubstituted heteroaryl group having from 20 to 20, a substituted or unsubstituted condensed polycyclic group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group or a carboxy group; p is an integer from 1 to 6; * Represents a bond.

According to another embodiment of the present invention, the heterocyclic compound may be one of the following compounds:

Figure pat00006

According to another aspect of the present invention, there is provided a plasma display panel comprising: a first electrode; A second electrode; And an organic light emitting device interposed between the first electrode and the second electrode, wherein the organic light emitting device includes a first layer including the heterocyclic compound.

According to an embodiment of the present invention, the first layer has a hole injection layer, a hole transport layer, a hole injection and a hole transport function at the same time having a functional layer, an electron injection layer, an electron transport layer, or an electron injection and electron transport function at the same time It may be a functional layer.

According to another embodiment of the present invention, the first layer has a hole injection layer, a hole transport layer, a hole injection and a hole transport function at the same time having a functional layer, a light emitting layer, an electron injection layer, an electron transport layer, or an electron injection and electron transport function At the same time having a functional layer, the first layer may further comprise a charge-generating material.

According to another embodiment of the present invention, the organic layer has a hole injection layer, a hole transport layer, a hole injection layer and a hole transport function at the same time, a functional layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer or a combination of two or more thereof It may further include.

According to another embodiment of the present invention, at least one of the hole injection layer, the hole transport layer, or a functional layer having both the hole injection function and the hole transport function may further include a charge-generating material.

According to another embodiment of the present invention, the light emitting layer may include a host and a dopant, and the dopant may be a fluorescent dopant or a phosphorescent dopant.

According to another embodiment of the present invention, the phosphorescent dopant may be an organometallic complex including Ir, Pt, Os, Re, Ti, Zr, Hf, or a combination of two or more thereof.

According to another embodiment of the present invention, the electron transport layer may include an electron transport organic material and a metal-containing material.

According to another embodiment of the invention, the metal-containing material may comprise a Li complex.

According to another embodiment of the present invention, the first layer of the organic light emitting device may be formed by a wet process using the heterocyclic compound.

According to still another aspect of the present invention, there is provided a flat panel display device including the organic light emitting device, wherein the first electrode of the organic light emitting device is electrically connected to a source electrode or a drain electrode of the thin film transistor.

The heterocyclic compound according to the embodiment of the present invention has excellent luminescence properties and charge transporting ability, and thus is useful as an electron injection material or an electron transporting material suitable for fluorescence and phosphorescent devices of almost all colors such as red, green, blue, and white. In particular, it is useful as a light emitting material of a green, blue, and white fluorescent device, and by using this, an organic electroluminescent device of high efficiency, low voltage, high brightness, and long life can be manufactured.

1 is a view showing the structure of an organic light emitting device according to an embodiment of the present invention.

Anthracene derivatives are well known as organic light emitting layer materials. For example, organic electroluminescent devices using dimers or trimers of phenylanthracene are known, but devices using such compounds contain two or three anthracenes linked through a conjugated system, resulting in a smaller energy gap. There was a problem that the color purity of blue light emission falls.

In addition, such a compound has a weak point which is easy to oxidize, and it is easy to produce an impurity, and there existed a point which was difficult in refinement | purification. In order to overcome this problem, an organic light emitting device using an anthracene compound substituted with 1,9-position with naphthalene or a diphenylanthracene compound substituted with an aryl group in the m-position of a phenyl group is known, but has a disadvantage of low luminous efficiency.

In addition, an organic light emitting device using a naphthalene-substituted monoanthracene derivative is known, but the luminous efficiency is not practical as low as 1 cd / A. In addition, an organic light emitting device using a compound having a phenylanthracene structure is known, but such a compound has excellent heat resistance because the m-position is substituted with an aryl group, but the luminous efficiency characteristic is about 2 cd / A, which is not satisfactory.

Hereinafter, the present invention will be described in detail.

According to one aspect of the present invention, a heterocyclic compound represented by Formula 1 is provided:

≪ Formula 1 >

Figure pat00007

In Formula 1, R 1 to R 13 are each independently a hydrogen atom, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, and having 2 to 60 carbon atoms. A substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, 5 carbon atoms An amino group substituted with a substituted or unsubstituted arylthio group having from 60 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, an aryl group having 5 to 60 carbon atoms or a heteroaryl group having 3 to 60 carbon atoms, and having 3 to 60 carbon atoms Substituted or unsubstituted heteroaryl group, substituted or unsubstituted condensed polycyclic group having 6 to 60 carbon atoms, halogen atom, cyano group, nitro group, hydroxy group or carboxy group, R 1 and R 2 are May be combined with each other to form an aromatic ring.

The heterocyclic compound according to an embodiment of the present invention has a function as a light emitting material, an electron transporting material or an electron injection material for an organic light emitting device. Compounds containing heterocycles in the molecule, such as the heterocyclic compound, have a high glass transition temperature (Tg) or melting point due to the introduction of a heterocycle. Therefore, the heat resistance of the organic layer in the electroluminescence, the interlayer between the organic layers, the luminescence generated between the organic layer and the metal electrode, and the resistance in a high temperature environment are increased.

The organic electroluminescent device manufactured using the heterocyclic compound according to the embodiment of the present invention has high durability during storage and driving.

The substituent of the said heterocyclic compound is explained in more detail.

According to an embodiment of the present invention, in Formula 1, R 1 , R 2 and R 8 are each independently a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, substituted or unsubstituted C 3 to 20 carbon atoms It may be a heteroaryl group, or a substituted or unsubstituted condensed polycyclic group having 5 to 20 carbon atoms.

According to an embodiment of the present invention, in Formula 1, R 3 to R 7 and R 9 to R 13 may be each independently hydrogen or deuterium.

According to another embodiment of the present invention, in Formula 1, R 1 and R 2 are each independently hydrogen, deuterium, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, or any one of the following Formulas 2a to 2e: Can be:

Figure pat00008

In Formulas 2a to 2e, Q 1 is a linking group represented by -C (R 14 ) (R 15 )-, -N (R 16 )-, -S- or -O-; Y 1 , Y 2 and Y 3 are independently of each other a linking group represented by -N =, -N (R 17 )-or -C (R 18 ) =; Z 1 , Z 2 , R 14 , R 15 , R 16 , R 17 and R 18 are each independently a hydrogen atom, deuterium, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, A substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted condensed polycyclic group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group or a carboxy group; p is an integer from 1 to 12; * Represents a bond.

According to another embodiment of the present invention, in Formula 1, R 8 may be any one of the following Formulas 3a to 3j:

Figure pat00009

In Formulas 3a to 3j, Q 1 is a linking group represented by -C (R 14 ) (R 15 )-, -N (R 16 )-, -S-, or -O-; Y 1 , Y 2 and Y 3 are independently of each other a linking group represented by —O—, —N =, —N (R 17 ) — or —C (R 18 ) =; Z 1 , Z 2 , Ar 12 , Ar 13 , R 14 , R 15 , R 16 , R 17 And R 18 independently of each other, a hydrogen atom, deuterium, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, and having 6 to 6 carbon atoms 20 substituted or unsubstituted condensed polycyclic group, halogen atom, cyano group, nitro group, hydroxy group or carboxy group; Ar 11 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 5 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms; p is an integer from 1 to 12; r is an integer from 0 to 5; * Represents a bond.

According to another embodiment of the present invention, in Formula 1, R 1 and R 2 are each independently hydrogen, deuterium, or any one of the following Formulas 4a to 4g, or may be bonded to each other to form a benzene ring. have:

Figure pat00010

In Formulas 4a to 4g, Z 1 and Z 2 independently of each other, a hydrogen atom, deuterium, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, a substituted or unsubstituted carbon atom 3 to 20 A substituted heteroaryl group, a substituted or unsubstituted condensed polycyclic group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group or a carboxy group; p is an integer from 1 to 6; * Represents a bond.

According to another embodiment of the present invention, in Formula 1, R 8 may be any one of the following Formulas 5a to 5o:

Figure pat00011

In Formulas 5a to 5o, Z 1 , Z 2 , Ar 12, and Ar 13 are each independently a hydrogen atom, deuterium, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, and 3 carbon atoms. A substituted or unsubstituted heteroaryl group having from 20 to 20, a substituted or unsubstituted condensed polycyclic group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group or a carboxy group; p is an integer from 1 to 6; * Represents a bond.

Hereinafter, the definition of a representative group among the groups used in the chemical formulas of the present invention is as follows (the number of carbons defining a substituent is not limited and does not limit the properties of the substituent).

In the above formula, unsubstituted carbon of 1 to 60 Alkyl groups may be linear and branched and non-limiting examples include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, heptyl, octyl, nonanyl, , At least one hydrogen atom of the alkyl group may be substituted with a substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, 1 to 10 carbon atoms Alkyl group, 1 to 10 carbon atoms Alkoxy group, 2 to 10 carbon atoms An alkenyl group having 2 to 10 carbon atoms An alkynyl group, an aryl group having 6 to 16 carbon atoms, or an aryl group having 4 to 16 carbon atoms And may be substituted with a heteroaryl group.

In the above formula, an unsubstituted alkenyl group having 2 to 60 carbon atoms means that it contains at least one carbon double bond in the middle or the end of the unsubstituted alkyl group. Examples include ethenyl, propenyl, butenyl, and the like. At least one hydrogen atom in these unsubstituted alkenyl groups may be substituted with the same substituent as in the case of the substituted alkyl group described above.

In the above formula, an unsubstituted alkynyl group having 2 to 60 carbon atoms means containing at least one carbon triple bond in the middle or at the end of the alkyl group as defined above. Examples include acetylene, propylene, phenylacetylene, naphthylacetylene, isopropylacetylene, t-butylacetylene, diphenylacetylene, and the like. At least one hydrogen atom in these alkynyl groups may be substituted with the same substituent as in the case of the substituted alkyl group described above.

In the above formula, an unsubstituted cycloalkyl group having 3 to 60 carbon atoms means an alkyl group having 3 to 60 carbon atoms, and at least one hydrogen atom of the cycloalkyl group is the same as the substituent of the alkyl group having 1 to 60 carbon atoms. Substitutable with a substituent.

In the above formula, an unsubstituted alkoxy group having 1 to 60 carbon atoms is -OA, wherein A is an unsubstituted carbon having 1 to 60 carbon atoms as described above. Alkyl group), examples of which include, but are not limited to, methoxy, ethoxy, propoxy, isopropyloxy, butoxy, pentoxy, and the like. At least one hydrogen atom of these alkoxy groups may be substituted with the same substituent as in the alkyl group described above.

In the above formula, an unsubstituted aryl group having 5 to 60 carbon atoms means a carbocycle aromatic system including one or more rings, and when having two or more rings, may be fused to each other or connected through a single bond or the like. The term aryl includes aromatic systems such as phenyl, naphthyl, anthracenyl. At least one of the hydrogen atoms of the aryl group may be substituted with the same substituent as the substituent of the alkyl group having 1 to 60 carbon atoms.

Examples of the substituted or unsubstituted aryl group having 5 to 60 carbon atoms include phenyl group and 1 to 10 carbon atoms. (E.g., o-, m- and p-fluorophenyl groups, dichlorophenyl groups), cyanophenyl groups, dicyanophenyl groups, trifluoromethoxyphenyl groups, biphenyl groups , A halobiphenyl group, a cyanobiphenyl group, a group having 1 to 10 carbon atoms An alkylphenyl group, an alkylphenyl group having 1 to 10 carbon atoms M, and p-tolyl groups, o-, m-, and p-cumenyl groups, mesityl groups, phenoxyphenyl groups, (?,? - dimethylbenzene) phenyl groups, Naphthyl group, halonaphthyl group (for example, fluoronaphthyl group) having 1 to 10 carbon atoms, a monovalent group having 1 to 10 carbon atoms Alkyl naphthyl group (for example, methyl naphthyl group), C1-C10 An acenaphthyl group, a phenaranyl group, a fluorenyl group, an anthraquinolyl group, a methylene group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, A phenanthryl group, a triphenylene group, a pyrenyl group, a chrysenyl group, an ethyl-chrysenyl group, a picenyl group, a perylenyl group, a chloroperylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, A phenyl group, a hexacenyl group, a rubicenyl group, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a pyranthrenyl group, and an obarenyl group.

In the above formula, an unsubstituted heteroaryl group having 3 to 60 carbon atoms includes 1, 2, or 3 heteroatoms selected from N, O, P, or S, and when they have two or more rings, they may be fused to each other or a single bond And so on. Unsubstituted 4 to 60 carbon atoms Examples of the heteroaryl group include a pyrazolyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, A benzoyl group, a carbazolyl group, an indolyl group, a quinolinyl group, an isoquinolinyl group, and a dibenzothiophen group. And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the substituent of the alkyl group having 1 to 60 carbon atoms.

In the above formula, an unsubstituted aryloxy group having 5 to 60 carbon atoms is a group represented by -OA 1 , wherein A 1 is an aryl group having 5 to 60 carbon atoms. Examples of the aryloxy group include a phenoxy group and the like. At least one hydrogen atom of the aryloxy group may be substituted with the same substituent as the substituent of the alkyl group having 1 to 60 carbon atoms.

In the formula, an unsubstituted arylthio group having 5 to 60 carbon atoms is a group represented by -SA 1 , where A 1 is an aryl group having 5 to 60 carbon atoms. Examples of the arylthio group include benzenethio group, naphthylthio group and the like. At least one hydrogen atom of the arylthio group may be substituted with the same substituent as the substituent of the alkyl group having 1 to 60 carbon atoms described above.

In the above formula, unsubstituted 6 to 60 carbon atoms The condensed polycyclic ring refers to a substituent containing two or more rings in which at least one aromatic ring and at least one non-aromatic ring are fused to each other or a substituent having an unsaturated group in the ring but not having a conjugated structure, Lt; RTI ID = 0.0 > and / or < / RTI > heteroaryl groups.

Hereinafter, specific examples of the compound represented by Chemical Formula 1 of the present invention include the following compounds 1 to 65. However, the heterocyclic compound according to one embodiment of the present invention should not be limited to these compounds.

Figure pat00012

Figure pat00013

Figure pat00014

Figure pat00015

Figure pat00016

An organic light emitting diode according to an embodiment of the present invention includes a first electrode; A second electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes a first layer including the heterocyclic compound.

The first layer including the heterocyclic compound may be a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, an electron injection layer, an electron transport layer, or a functional layer having an electron injection function and an electron transport function at the same time. Can be.

According to one embodiment of the invention, the first layer is a functional layer having a hole injection layer, a hole transport layer, a hole injection and a hole transport function at the same time, a light emitting layer, an electron injection layer, an electron transport layer, or an electron injection and electron transport function At the same time having a functional layer, the first layer may further comprise a charge-generating material.

The charge-generating material will be described later.

The organic layer of the organic light emitting device according to an embodiment of the present invention is a functional layer having a hole injection layer, a hole transport layer, a hole injection layer and a hole transport function at the same time, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer or the It may further include a combination of two or more, but is not limited thereto. At least one of the hole injection layer, the hole transport layer, or a functional layer having the hole injection function and the hole transport function at the same time, a heterocyclic compound, a known hole injection material and a known hole transport material according to an embodiment of the present invention In addition, a charge-generating material may be further included to improve conductivity of the film. The light emitting layer, which may be further included, includes a host and a dopant, and the dopant may be a fluorescent dopant or a phosphorescent dopant, and the phosphorescent dopant may be Ir, Pt, Os, Re, Ti, Zr, Hf, or a combination of two or more thereof. It may include.

The charge-generating material may be, for example, a p-dopant. Non-limiting examples of the p-dopant include tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4TCNQ) Quinone derivatives such as these; Metal oxides such as tungsten oxide and molybdenum oxide; And cyano group-containing compounds such as Compound 100, and the like, but are not limited thereto.

<Compound 100>

Figure pat00017

When the hole injection layer, the hole transport layer, or the functional layer having the hole injection function and the hole transport function at the same time further include the charge-generating material, the charge-generating material is uniformly dispersed or non-uniform in the layers. Various modifications are possible, such as may be distributed.

The electron transport layer of the organic light emitting device according to the embodiment of the present invention may include an electron transport organic compound and a metal-containing material. Non-limiting examples of the electron transporting organic compound include ADN (9,10-di (naphthalen-2-yl) anthracene); And anthracene-based compounds such as Compounds 101 and 102, but are not limited thereto.

<Compound 101> <Compound 102>

Figure pat00018
Figure pat00019

The metal-containing material may comprise a Li complex. Non-limiting examples of the Li complex include lithium quinolate (LiQ) or the following compound 103:

<Compound 103>

Figure pat00020

Meanwhile, the first electrode may be an anode and the second electrode may be a cathode, and vice versa.

For example, the organic light emitting device according to the embodiment of the present invention, the first electrode / hole injection layer / light emitting layer / second electrode, the first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / second electrode Or a first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / second electrode structure. Alternatively, the organic light emitting device may be a functional layer / light emitting layer / electron transport layer / second electrode having a first electrode / hole injection function and a hole transport function at the same time, or a functional layer / light emitting layer having a first electrode / hole injection function and a hole transport function at the same time. / Electron transport layer / electron injection layer / second electrode structure. Alternatively, the organic light emitting device has a functional layer / second electrode having a first electrode / hole transporting layer / light emitting layer / electron injection and electron transporting functions and a first electrode / hole injection layer / light emitting layer / electron injection and electron transporting functions simultaneously. It may have a functional layer / second electrode, or a functional layer / second electrode structure having a first electrode / hole injection layer / hole transport layer / light emitting layer / electron injection and electron transport function at the same time.

The organic light emitting device according to the embodiment of the present invention can be applied in various structures such as a top emission type, a bottom emission type.

Hereinafter, a method of manufacturing an organic light emitting diode according to the present invention will be described with reference to the organic light emitting diode illustrated in FIG. 1. 1 includes a substrate, a first electrode (anode), a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a second electrode (cathode).

First, the first electrode material having a high work function on the substrate is formed by vapor deposition, sputtering, or the like to form the first electrode. The first electrode may be an anode or a cathode. Herein, a substrate used in a conventional organic light emitting device is used, and a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness is preferable. As the first electrode material, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), Al, Ag, Mg and the like having excellent conductivity may be used. Or a reflective electrode.

Next, a hole injection layer HIL may be formed on the first electrode by using various methods such as vacuum deposition, spin coating, casting, and LB.

When the hole injection layer is formed by vacuum deposition, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the hole injection layer, and the like. It is preferable to select suitably in the range of a vacuum degree of 10 -8 to 10 -3 torr and a deposition rate of 0.01 to 100 kPa / sec.

When the hole injection layer is formed by the spin coating method, the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal characteristics of the desired hole injection layer, but the coating speed is about 2000 rpm to 5000 rpm. , The heat treatment temperature for removing the solvent after coating is preferably selected in the temperature range of about 80 ℃ to 200 ℃.

As the hole injection layer material, a heterocyclic compound according to an embodiment of the present invention as described above may be used, or a known hole injection material may be used, for example, a phthalocyanine compound such as copper phthalocyanine, m -MTDATA [4,4 ', 4' '-tris (3-methylphenylphenylamino) triphenylamine], NPB (N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine (N, N'- di (1-naphthyl) -N, N'-diphenylbenzidine)), TDATA, 2T-NATA, Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid: polyaniline / dodecylbenzenesulfonic acid), PEDOT / PSS (Poly (3,4-ethylenedioxythiophene) ) / Poly (4-styrenesulfonate): Poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate)), Pani / CSA (Polyaniline / Camphor sulfonicacid: polyaniline / camphorsulfonic acid) or PANI / PSS ( Polyaniline) / Poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate)) and the like may be used, but is not limited thereto.

Figure pat00021
Figure pat00022
Figure pat00023

The thickness of the hole injection layer may be about 100 Å to 10000 Å, preferably 100 Å to 1000 Å. When the thickness of the hole injection layer satisfies the above range, excellent hole injection characteristics may be obtained without increasing a driving voltage.

Next, a hole transport layer (HTL) may be formed on the hole injection layer by using various methods such as vacuum deposition, spin coating, cast, and LB. In the case of forming the hole transport layer by vacuum deposition and spin coating, the deposition conditions and coating conditions vary depending on the compound used, but are generally selected from the ranges of conditions substantially the same as those of forming the hole injection layer.

The hole transport layer material may use a heterocyclic compound according to an embodiment of the present invention as described above, or may use a known hole transport layer material, for example, N-phenylcarbazole, polyvinylcarbazole, etc. Aromatic condensed rings such as carbazole derivatives, NPB, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-biphenyl] -4,4'-diamine (TPD) Amine derivatives having the like and the like can be used.

Figure pat00024
Figure pat00025

The hole transport layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 600 kPa. When the thickness of the hole transport layer satisfies the above range, excellent hole transport characteristics may be obtained without a substantial increase in driving voltage.

Next, an emission layer (EML) may be formed on the hole transport layer by using a method such as vacuum deposition, spin coating, casting, and LB. When the light emitting layer is formed by a vacuum deposition method or a spin coating method, the deposition conditions vary depending on the compound used, but are generally selected from a range of conditions almost the same as that of forming the hole injection layer.

The light emitting layer may include a heterocyclic compound according to an embodiment of the present invention as described above. The light emitting layer may be formed using various known light emitting materials, and may be formed using a known host and a dopant. In the case of the above-mentioned dopant, a known fluorescent dopant and a known phosphorescent dopant can be used.

For example, known hosts include Alq 3 , CBP (4,4'-N, N'-dicarbazole-biphenyl), PVK (poly (n-vinylcarbazole)), 9,10-di (naphthalene -2-yl) anthracene (ADN), TCTA, TPBI (1,3,5-tris (N-phenylbenzimidazol-2-yl) benzene (1,3,5-tris (N-phenylbenzimidazole-2-yl ) benzene)), TBADN (3-tert-butyl-9,10-di (naphth-2-yl) anthracene), E3, DSA (distyrylarylene) and the like can be used, but is not limited thereto.

Figure pat00026
Figure pat00027

Figure pat00028

Figure pat00029

      PVK

On the other hand, PtOEP, Ir (piq) 3 , Btp 2 Ir (acac), DCJTB and the like can be used as a known red dopant, but is not limited thereto.

Figure pat00030

Ir (ppy) 3 (ppy = phenylpyridine), Ir (ppy) 2 (acac), Ir (mpyp) 3 and C545T may be used as the known green dopant. However, the present invention is not limited thereto.

Figure pat00031

Figure pat00032

      C545T

On the other hand, a blue dopant known as a blue dopant is F 2 Irpic, (F 2 ppy) 2 Ir (tmd), Ir (dfppz) 3 , ter-fluorene, 4,4′-bis (4-diphenyl Aminostaryl) biphenyl (DPAVBi), 2,5,8,11-tetra- ti -butyl perylene (TBP), and the like, but are not limited thereto.

Figure pat00033

Figure pat00034
Figure pat00035

               DPAVBi TBP

The content of the dopant is preferably 0.1 to 20 parts by weight, particularly 0.5 to 12 parts by weight, based on 100 parts by weight of the light emitting layer forming material (ie, the total weight of the host and the dopant is 100 parts by weight). When the content of the dopant satisfies the above range, concentration quenching phenomenon can be substantially prevented.

The thickness of the light emitting layer may be about 100 Å to 1000 Å, preferably 200 Å to 600 Å. When the thickness of the light emitting layer satisfies the above range, excellent light emission characteristics may be obtained without a substantial increase in driving voltage.

When the light emitting layer includes a phosphorescent dopant, a hole blocking layer HBL may be formed on the light emitting layer to prevent the triplet excitons or holes from diffusing into the electron transport layer (not shown in FIG. 1). The hole blocking layer material that can be used at this time is not particularly limited, and may be selected arbitrarily from known hole blocking layer materials. For example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, Balq, BCP, and the like can be used.

The hole blocking layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 300 kPa. This is because when the thickness of the hole blocking layer is less than 50 kV, the hole blocking property may be deteriorated, and when the thickness of the hole blocking layer is more than 1000 kV, the driving voltage may increase.

Next, the electron transport layer (ETL) is formed by various methods such as vacuum deposition, spin coating, casting or the like. In the case of forming the electron transporting layer by the vacuum deposition method and the spin coating method, the conditions vary depending on the compound to be used, but are generally selected from the ranges of conditions substantially the same as those of forming the hole injection layer.

The electron transport layer material may be a heterocyclic compound according to an embodiment of the present invention as described above. Or any known electron transport layer forming material. For example, a quinoline derivative, in particular, a known material such as tris (8-quinolinorate) aluminum (Alq 3 ), TAZ, Balq and the like may be used, but is not limited thereto.

Figure pat00036
Figure pat00037

The electron transport layer may have a thickness of about 100 kPa to 1000 kPa, preferably 100 kPa to 500 kPa. When the thickness of the electron transport layer satisfies the above range, excellent electron transport characteristics can be obtained without a substantial increase in driving voltage.

In addition, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer.

As the electron injection layer, any material known as a heterocyclic compound according to one embodiment of the present invention as described above or an electron injection layer forming material such as LiF, NaCl, CsF, Li 2 O, BaO, or the like may be used. Although the deposition conditions and coating conditions of the electron injection layer vary depending on the compound used, they are generally selected from the range of conditions almost the same as the formation of the hole injection layer.

The electron injection layer may have a thickness of about 1 kPa to 100 kPa, preferably 5 kPa to 90 kPa. When the thickness of the electron injection layer satisfies the above range, excellent electron injection characteristics may be obtained without a substantial increase in driving voltage.

Finally, the second electrode can be formed on the electron injection layer by using a method such as vacuum deposition or sputtering. The second electrode may be used as a cathode or an anode. As the material for forming the second electrode, a metal, an alloy, an electrically conductive compound having a low work function, or a mixture thereof may be used. Specific examples thereof include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- . In addition, it is also possible to use a transparent cathode using ITO, IZO to obtain a top light emitting device.

The organic light emitting device according to the present invention may be provided in various types of flat panel display devices, for example, a passive matrix organic light emitting display device and an active matrix organic light emitting display device. In particular, when provided in the active matrix organic light emitting display device, the first electrode provided on the substrate side may be electrically connected to the source electrode or the drain electrode of the thin film transistor as the pixel electrode. In addition, the organic light emitting device may be provided in a flat panel display device capable of displaying a screen on both sides.

In addition, the first layer of the organic light emitting device according to an embodiment of the present invention may be formed by a deposition method using a heterocyclic compound according to an embodiment of the present invention, or in one embodiment of the present invention prepared in solution It can also be formed by a wet method of coating a heterocyclic compound according to.

Hereinafter, the present invention specifically illustrates preferred synthesis examples and examples of the compounds 3, 8, 18, 37, 53 and 65, but does not mean that the present invention is limited to the following examples.

[Example]

Figure pat00038

Synthetic example  One.  Synthesis of Compound 3

Synthesis of Intermediate I-1

2.43 g (10 mmol) of 6-Aminochrysene and 760 mg (10 mmol) of 1,3-propane diol were dissolved in 10 ml of mesitylene. 0.240 g (0.4 mmol) IrCl 3 H 2 O, 36 mg (0.6 mmol) BINAP (2,2'-bis-diphenylphosphino-1,1'-binaphtyl) and 0.064 g (0.6 mmol) Na 2 CO 3 Was added and stirred at 170 ° C. for 15 hours. The filtrate was concentrated and the residue was purified by silica gel column chromatography to give 2.56 g yield 92% of intermediate I-1). The resulting compound was confirmed by LC / MS.

C 21 H 13 N calc .: 279.1; Found [M + 1] 280.1

Synthesis of Intermediate I-2

4.19 g (15.0 mmol) of Intermediate I-1 are dissolved in 100 ml of dichloromethane, and 1.75 ml (15.0 mmol) of bromine (Br 2 ) is slowly added dropwise at 0 ° C. The reaction solution was stirred at room temperature for 12 hours. 60 mL of water and 30 ml of a 20% aqueous solution of sodium thiosulfate were added to the reaction solution, followed by extraction three times with 80 mL of dichloromethane. The combined organic layers were dried over magnesium sulfate, the solvent was evaporated, the residue was separated and purified by silica gel column chromatography, and recrystallized with a dichloromethane / hexane solution to obtain 3 g of Intermediate I-2 (yield 56%). The resulting compound was confirmed by LC-MS. C 21 H 12 BrN calc .: 357.0; Found [M + 1] 358.0

Figure pat00039

Synthesis of Intermediate I-3

4-Bromopyridine 3.16 g (20.0 mmol), aniline 2.79 g (30.0 mmol), Pd 2 (dba) 3 0.37 g (0.4 mmol), P t Bu 3 0.08 g (0.4 mmol) and KO t Bu 2.88 g (30.0 mmol) was dissolved in 60 ml of toluene and stirred at 85 ° C. for 4 hours. The reaction solution was cooled to room temperature, and then extracted three times with 50 mL of water and 50 mL of diethyl ether. The combined organic layers were dried over magnesium sulfate, and the residue obtained by evaporation of the solvent was separated and purified through silica gel column chromatography to obtain 1.49 g (yield 88%) of intermediate I-3. The resulting compound was confirmed by LC-MS. C 11 H 10 N calc .: 170.1; Found [M + 1] 171.1

Synthesis of intermediate I-4

Intermediate I-3 2.55 g (15.0 mmol), 2-bromoiodobenzene 2.83 g (10.0 mmol), Pd 2 (dba) 3 0.18 g (0.2 mmol), P t Bu 3 0.04 g (0.4 mmol) and KO t Bu 1.44 g (15.0 mmol) was dissolved in 40 ml of toluene and stirred at 85 ° C. for 4 hours. The reaction solution was cooled to room temperature, and then extracted three times with 30 mL of water and 30 mL of diethyl ether. The combined organic layers were dried over magnesium sulfate, and the residue obtained by evaporation of the solvent was separated and purified by silica gel column chromatography to obtain 2.04 g of Intermediate I-4 (yield 63%). The resulting compound was confirmed by LC-MS. C 17 H 13 BrN 2 calc .: 324.0; Found [M + 1] 325.0

Synthesis of Intermediate I-5

3.25 g (10.0 mmol) of Intermediate I-4, 2.54 g (10.0 mmol) of Bis (pinacolato) diborone, 0.36 g (0.5 mmol) of PdCl 2 (dppf) 2 and 2.94 g (30.0 mmol) of KOAc were dissolved in 40 ml of DMSO. Stir at 80 ° C. for 6 hours. The reaction solution was cooled to room temperature, and then extracted three times with 50 mL of water and 50 mL of diethyl ether. The combined organic layers were dried over magnesium sulfate, and the residue obtained by evaporation of the solvent was separated and purified through silica gel column chromatography to obtain 2.97 g (yield 80%) of Intermediate I-5. The resulting compound was identified via LC-MS. C 23 H 25 BN 2 O 2 calc .: 372.2; Found [M + 1] 373.2

compound 3 of  synthesis

1.79 g (5.0 mmol) of intermediate I-2, 1.86 g (5.0 mmol) of intermediate I-5, 0.29 g (0.25 mmol) of Pd (PPh 3 ) 4 , and K 2 CO 3 2.07 g (15.0 mmol) was dissolved in 30 ml of a THF / H 2 O (2/1) mixed solution and stirred at 70 ° C. for 5 hours. The reaction solution was cooled to room temperature, and then extracted three times with 50 mL of water and 50 mL of diethyl ether. The combined organic layer was dried over magnesium sulfate, and the residue obtained by evaporation of the solvent was separated and purified by silica gel column chromatography to obtain 1.49 g (yield 69%) of compound 3. The resulting compound was confirmed by HR-MS. C 32 H 20 N 2 calcd: 432.1626; Found [M + 1] 437.1626

1 H NMR (CDCl 3 , 400 MHz) δ (ppm) 9.59-9.54 (m, 1H), 9.02 (s, 1H), 8.90-8.89 (d, 1H), 8.83 (d, 1H), 8.75-8.74 (d , 2H), 8.69-8.67 (m, 1H), 8.25-8.23 (d, 1H), 8.10 (d, 1H), 7.88-7.86 (d, 1H), 7.84-7.81 (m, 2H), 7.71-7.67 (m, 2H), 7.60-7.58 (m, 1H), 7.55-7.53 (d, 2H), 7.42-7.40 (dd, 1H), 7.36-7.32 (t, 1H), 7.19-7.15 (t, 1H)

Synthetic example  2.  Synthesis of Compound 8

Figure pat00040

Synthesis of Intermediate I-6

2.86 g (80% yield) of intermediate I-6 were obtained using 3,3 '-(5-bromo-1,3-phenylene) dipyridine in the same manner as the synthesis of intermediate I-5. The resulting compound was identified via LC-MS. C 22 H 23 BN 2 0 2 calc .: 358.2; Found [M + 1] 359.2

Synthesis of Compound 8

Compound 8 was synthesized using intermediate I-2 and intermediate I-6 in the same manner as the synthesis of compound 3. The resulting compound was confirmed by HR-MS. C 37 H 23 N 3 calcd .: 509.1892; Found [M + 1] 510.1892

1 H NMR (CDCl 3 , 400 MHz) δ (ppm) 9.59-9.54 (m, 1H), 8.95 (m, 3H), 8.90-8.89 (d, 1H), 8.83-8.80 (d, 1H), 8.72-8.66 (m, 3H), 8.40-8.38 (d, 1H), 8.10-8.08 (m, 3H), 8.04 (s, 2H), 7.90-7.89 (d, 1H), 7.84-7.80 (m, 2H), 7.71 -7.67 (t, 1H), 7.50-7.46 (dd, 2H), 7.42-7.39 (dd, 1H), 7.25-7.21 (t, 1H))

Synthetic example  3.  Synthesis of Compound 18

Figure pat00041

Synthesis of Intermediate I-7

3.09 g (yield 78%) of intermediate I-7 was obtained using 2- (4-bromophenyl) -1-phenyl-benzoimidazole in the same manner as the synthesis of intermediate I-5. The resulting compound was identified via LC-MS. C 25 H 25 BN 2 0 2 calc .: 396.3; Found [M + 1] 397.3

Synthesis of Compound 18

Compound 18 1.93 g (yield 71%) was obtained using intermediate I-2 and intermediate I-7 in the same manner as in the synthesis of compound 3. The resulting compound was confirmed by HR-MS. C 40 H 25 N 3 calc .: 547.6466; Found [M + 1] 548.6466

1 H NMR (CDCl 3 , 400 MHz) δ (ppm) 9.59-9.54 (m, 1H), 9.09 (s, 1H), 8.90-8.89 (d, 1H), 8.83-8.82 (m, 2H), 8.71-8.67 (m, 1H), 8.20-8.17 (d, 2H), 7.85-7.82 (m, 5H), 7.80-7.78 (d, 1H), 7.71-7.66 (dd, 2H), 7.57-7.52 (m, 2H) , 7.44-7.37 (m, 4H), 7.30 (t, 1H), 7.24-7.21 (t, 1H), 7.16-7.13 (t, 1H))

Synthetic example  4.  Synthesis of Compound 37

Figure pat00042

Synthesis of Intermediate I-8

Intermediate I-2 1.79 g (5.0 mmol), 2-naphtalene boronic acid 0.85 g (5.0 mmol), Pd (PPh 3 ) 4 0.29 g (0.25 mmol), and K 2 CO 3 2.07 g (15.0 mmol) was dissolved in 30 ml of a THF / H 2 O (2/1) mixed solution and stirred at 70 ° C. for 5 hours. The reaction solution was cooled to room temperature, and then extracted three times with 50 mL of water and 50 mL of diethyl ether. The combined organic layers were dried over magnesium sulfate, and the residue obtained by evaporation of the solvent was separated and purified through silica gel column chromatography to obtain 1.78 g (yield 88%) of intermediate I-8. The resulting compound was identified via LC-MS. C 31 H 19 N calc .: 405.2; Found [M + 1] 406.2

Synthesis of Intermediate I-9

6.08 g (15.0 mmol) of Intermediate I-8 are dissolved in 100 ml of dichloromethane, and 1.75 ml (15.0 mmol) of bromine (Br 2 ) is slowly added dropwise at 0 ° C. The reaction solution was stirred at room temperature for 12 hours. 60 mL of water and 30 ml of a 20% aqueous solution of sodium thiosulfate were added to the reaction solution, followed by extraction three times with 80 mL of dichloromethane. The combined organic layers were dried over magnesium sulfate, the solvent was evaporated, the residue was separated and purified by silica gel column chromatography, and recrystallized with a dichloromethane / hexane solution to obtain 3.77 g (52%) of an intermediate I-9. The resulting compound was confirmed by LC-MS. C 31 H 18 BrN calc .: 483.1; Found [M + 1] 484.1

Figure pat00043

Synthesis of Intermediate I-10

6.28 g (yield 81%) of intermediate I-10 were obtained using 6-bromo-3,4'-bipyridine in the same manner as the synthesis of intermediate I-5. The resulting compound was identified via LC-MS. C 16 H 19 BN 2 O 2 calc .: 282.2; Found [M + 1] 283.2

Synthesis of Compound 37

2.09 g (yield 75%) of compound 37 was obtained using intermediate I-2 and intermediate I-7 in the same manner as the synthesis of compound 3. The resulting compound was confirmed by HR-MS. C 41 H 25 N 3 calc .: 559.2048; Found [M + 1] 560.2048

1 H NMR (CDCl 3 , 400 MHz) δ (ppm) 9.78-9.74 (m, 1H), 9.68 (s, 1H), 9.38 (d, 1H), 9.16 (d, 1H), 9.12 (s, 1H), 8.75-8.71 (m, 1H), 8.67-8.65 (m, 2H), 8.32-8.30 (d, 1H), 8.21-8.19 (d, 1H), 8.15 (s, 1H), 8.05-8.03 (d, 1H ), 8.00-7.98 (d, 1H), 7.88-7.81 (m, 6H), 7.73-7.69 (t, 1H), 7.60-7.52 (m, 2H), 7.43-7.41 (d, 2H), 7.19-7.15 (t, 1H)

Synthetic example  5.  Synthesis of Compound 53

Figure pat00044

Synthesis of Intermediate I-11

1.87 g (yield 78%) of intermediate I-11 was obtained using 2-pyrene boronic acid instead of 2-naphtalene boronic acid in the same manner as intermediate I-8. The resulting compound was identified via LC-MS. C 37 H 23 N calc .: 481.2; Found [M + 1] 482.2

Synthesis of Intermediate I-12

4.62 g of intermediate I-12 (yield 55%) was obtained using intermediate I-11 in the same manner as intermediate I-9. The resulting compound was confirmed by LC-MS. C 37 H 22 BrN calc .: 559.1; Found [M + 1] 560.1

Synthesis of Compound 53

Using the intermediate I-7 and the intermediate I-12 in the same manner as the synthesis of the compound 3, 2.61 g (yield 70%) of compound 53 was obtained. The resulting compound was confirmed by HR-MS. C 56 H 33 N 3 calcd: 747.2674; Found [M + 1] 748.2674

1 H NMR (CDCl 3 , 400 MHz) δ (ppm) 9.78-9.73 (m, 1H), 9.14 (s, 1H), 9.09 (s, 1H), 9.04 (s, 1H), 8.75-8.70 (m, 1H ), 8.49-8.47 (d, 1H), 8.41 (s, 2H), 8.23-8.21 (d, 2H), 8.16-8.14 (m, 2H), 8.10-8.02 (m, 4H), 7.96-7.94 (d , 2H), 7.85-7.78 (m, 4H), 7.73-7.69 (t, 1H), 7.66-7.64 (d, 1H), 7.57-7.52 (m, 2H), 7.44-7.35 (m, 4H), 7.32 -7.28 (t, 1H), 7.25-7.21 (t, 2H)

Synthetic example  6.  Synthesis of Compound 65

Figure pat00045

Synthesis of Intermediate I-13

2- (pyridine-4-yl) -4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-instead of 2-naphtalene boronic acid in the same way as for intermediate I-8 1,3,5-tetrazine was used to obtain 1.54 g (71% yield) of intermediate I-13. The resulting compound was identified via LC-MS. C 29 H 17 N 5 calcd for 435.1; Found [M + 1] 436.1

Synthesis of Intermediate I-14

Intermediate I-13 was obtained in the same manner as the intermediate I-9 to obtain 4.78 g of the intermediate I-14 (yield 62%). The resulting compound was confirmed by LC-MS. C 29 H 16 BrN 5 calc: 513.1; Found [M + 1] 514.1

Synthesis of Compound 65

In the same manner as in the synthesis of compound 3, compound 65, 2.16 g (yield 77%) was obtained using intermediate I-4 and 2-naphtalene boronic acid. The resulting compound was confirmed by HR-MS. C 39 H 23 N 5 calcd .: 561.1953; Found [M + 1] 562.1953

1 H NMR (CDCl 3 , 400 MHz) δ (ppm) 9.78-9.74 (m, 1H), 9.68 (s, 1H), 9.49 (s, 1H), 9.13 (s, 1H), 9.05-9.04 (m, 2H ), 8.91-8.88 (m, 1H), 8.83-8.81 (m, 2H), 8.70-8.68 (d, 1H), 8.35-8.34 (m, 2H), 8.13 (s, 1H), 8.01-7.97 (t , 2H), 7.90-7.80 (m, 5H), 7.64-7.58 (dd, 2H), 7.53-7.49 (m, 1H)

Example  One

The anode cut corning 15Ω / cm2 (1200Å) ITO glass substrate into 50mm x 50mm x 0.7mm size and ultrasonically cleaned for 5 minutes with isopropyl alcohol and pure water, and then irradiated with ultraviolet rays for 30 minutes and ozone The glass substrate was installed in a vacuum deposition apparatus after exposure to cleaning.

First, 2-TNATA, a known material as a hole injection layer, was vacuum deposited on the substrate to form a thickness of 600 Å, followed by 4,4'-bis [N- (1-naphthyl), which is a known material as a hole transport compound. ) -N-phenylamino] biphenyl (hereinafter referred to as NPB) was vacuum deposited to a thickness of 300 mm 3 to form a hole transport layer.

Figure pat00046

1,4-bis, a known compound as a blue fluorescent dopant, using 9,10-di-naphthalene-2-yl-anthracene (hereinafter referred to as ADN), a known compound, as a known blue fluorescent host on the hole transport layer. -(2,2-diphenylvinyl) biphenyl (hereinafter referred to as DPVBi) was co-deposited at a weight ratio of 98: 2 to form a light emitting layer having a thickness of 300 Pa.

Subsequently, the compound 3 of the present invention was deposited to an electron transport layer on the light emitting layer to a thickness of 300Å, then LiF, an alkali metal halide, was deposited on the electron transport layer to a thickness of 10Å on the electron injection layer, and Al was 3000Å (cathode electrode). The organic EL device was manufactured by vacuum deposition to a thickness of) to form a LiF / Al electrode.

The device exhibited a high luminance of 6.20 V and a light emission luminance of 2187 cd / m 2 at a current density of 50 mA / cm 2, a light emission efficiency of 4.37 cd / A, and a half life of 215 hours at 100 mA / cm 2 .

Example  2

An organic EL device was manufactured in the same manner as in Example 1, except that Compound 8 was used instead of Compound 3 to form an electron transport layer.

The device had a high luminance of driving voltage 6.38 V and emission luminance 2295 cd / m 2 at a current density of 50 mA / cm 2, an emission efficiency of 4.53 cd / A, and a half life of 226 hours at 100 mA / cm 2 .

Example  3

An organic EL device was manufactured in the same manner as in Example 1, except that Compound 18 was used instead of Compound 3 to form an electron transport layer.

The device exhibited a high luminance of driving voltage 6.46 V and a light emission luminance of 2005 cd / m 2 at a current density of 50 mA / cm 2, a light emission efficiency of 4.67 cd / A, and a half life of 235 hours at 100 mA / cm 2 .

Example  4

An organic EL device was manufactured in the same manner as in Example 1, except that Compound 37 was used instead of Compound 3 to form an electron transport layer.

The device had a high luminance of a driving voltage of 6.24 V and an emission luminance of 2443 cd / m 2 at a current density of 50 mA / cm 2, an emission efficiency of 4.86 cd / A, and a half life of 221 hours at 100 mA / cm 2 .

Example  5

An organic EL device was manufactured in the same manner as in Example 1, except that Compound 53 was used instead of Compound 3 when forming an electron transport layer.

The device had a high luminance of 6.18 V and a light emission luminance of 2758 cd / m 2 at a current density of 50 mA / cm 2, a light emission efficiency of 5.51 cd / A, and a half life of 275 hours at 100 mA / cm 2 .

Example  6

An organic EL device was manufactured in the same manner as in Example 1, except that Compound 65 was used instead of Compound 3 to form an electron transport layer.

The device exhibited a high luminance of 6.45 V of drive voltage and 2682 cd / m 2 of light emission at a current density of 50 mA / cm 2, a light emission efficiency of 5.36 cd / A, and a half life of 242 hours at 100 mA / cm 2 .

Comparative example  One

An organic EL device was manufactured in the same manner as in Example 1, except that Alq 3 , a known material, was used instead of the compound 3 in forming the electron transport layer.

The device exhibited a high luminance of 7.85 V and a light emission luminance of 1560 cd / m 2 at a current density of 50 mA / cm 2, a luminous efficiency of 3.12 cd / A, and a half life of 113 hours at 100 mA / cm 2 .

As a result of using the compounds according to one embodiment of the present invention as an electron transporting material and also as an electron transporting material in an organic electroluminescent device, the driving voltage was lowered by 1 V or more compared with Alq 3 , which is a known material. This improved excellent IVL characteristics and excellent brightness and life improvement effect.

Table 1 below summarizes the device characteristics and life results of the respective embodiments.

Electronic transport material Driving voltage
(V)
Current density
(㎃ / ㎠)
Luminance
(cd / ㎡)
efficiency
(cd / A)
Luminous color Half Life 명 (hr @ 100㎃ / ㎠)
Example 1 Compound 3 6.20 50 2,187 4.37 blue 215 hr Example 2 Compound 8 6.38 50 2,295 4.53 blue 226 hr Example 3 Compound 18 6.46 50 2,005 4.67 blue 235 hr Example 4 Compound 37 6.24 50 2,443 4.89 blue 221 hr Example 5 Compound 53 6.18 50 2,758 5.51 blue 275 hr Example 6 Compound 65 6.45 50 2,682 5.36 blue 242 hr Comparative Example 1 Alq 3 7.85 50 1,560 3.12 blue 113 hr

Although the present invention has been described with reference to the synthesis examples and examples, this is merely illustrative, and those skilled in the art to which the present invention pertains various modifications and equivalent other embodiments. Will understand. Accordingly, the true scope of the present invention should be determined by the technical idea of the appended claims.

Claims (19)

  1. A heterocyclic compound represented by the following formula (1):
    &Lt; Formula 1 >
    Figure pat00047

    In Formula 1,
    R 1 to R 13 are each independently a hydrogen atom, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted group having 2 to 60 carbon atoms Alkynyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 60 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 60 carbon atoms, substituted or unsubstituted aryloxy groups having 5 to 60 carbon atoms, substituted or substituted with 5 to 60 carbon atoms, or Unsubstituted arylthio groups, substituted or unsubstituted aryl groups having 5 to 60 carbon atoms, amino groups substituted with aryl groups having 5 to 60 carbon atoms or heteroaryl groups having 3 to 60 carbon atoms, substituted or unsubstituted with 3 to 60 carbon atoms Heteroaryl group, substituted or unsubstituted condensed polycyclic group having 6 to 60 carbon atoms, halogen atom, cyano group, nitro group, hydroxy group or carboxyl group,
    R 1 and R 2 may be bonded to each other to form an aromatic ring.
  2. The method of claim 1,
    In Formula 1, R 1 , R 2 and R 8 are each independently a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or 5 to 20 carbon atoms. A heterocyclic compound which is a substituted or unsubstituted condensed polycyclic group of.
  3. The method of claim 1,
    In Formula 1, R 3 to R 7 and R 9 to R 13 are each independently hydrogen or deuterium heterocyclic compound.
  4. The method of claim 1,
    In Formula 1, R 1 and R 2 are each independently hydrogen, deuterium, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, or a heterocyclic compound having any one of the following Formulas 2a to 2e:
    Figure pat00048

    In Formulas 2a to 2e,
    Q 1 are the linking groups represented by —C (R 14 ) (R 15 ) —, —N (R 16 ) —, —S— or —O—;
    Y 1 , Y 2 and Y 3 are independently of each other a linking group represented by -N =, -N (R 17 )-or -C (R 18 ) =;
    Z 1 , Z 2 , R 14 , R 15 , R 16 , R 17 And R 18 independently of each other, a hydrogen atom, deuterium, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, and having 6 to 6 carbon atoms 20 substituted or unsubstituted condensed polycyclic group, halogen atom, cyano group, nitro group, hydroxy group or carboxy group;
    p is an integer from 1 to 12;
    * Represents a bond.
  5. The method of claim 1,
    In Formula 1, R 8 is a heterocyclic compound of any one of Formulas 3a to 3j:
    Figure pat00049

    In Formulas 3a to 3j,
    Q 1 are the linking groups represented by —C (R 14 ) (R 15 ) —, —N (R 16 ) —, —S— or —O—;
    Y 1 , Y 2 and Y 3 are independently of each other a linking group represented by —O—, —N =, —N (R 17 ) — or —C (R 18 ) =;
    Z 1 , Z 2 , Ar 12 , Ar 13 , R 14 , R 15 , R 16 , R 17 And R 18 independently of each other, a hydrogen atom, deuterium, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, and having 6 to 6 carbon atoms 20 substituted or unsubstituted condensed polycyclic group, halogen atom, cyano group, nitro group, hydroxy group or carboxy group;
    Ar 11 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 5 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms;
    p is an integer from 1 to 12;
    r is an integer from 0 to 5;
    * Represents a bond.
  6. The method of claim 1,
    In Formula 1, R 1 and R 2 are each independently hydrogen, deuterium, any one of the following Formulas 4a to 4g, or a heterocyclic compound which is bonded to each other to form a benzene ring:
    Figure pat00050

    In Formulas 4a to 4g,
    Z 1 and Z 2 are each independently a hydrogen atom, deuterium, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, and carbon atoms 6 to 20 substituted or unsubstituted condensed polycyclic group, halogen atom, cyano group, nitro group, hydroxy group or carboxy group;
    p is an integer from 1 to 6;
    * Represents a bond.
  7. The method of claim 1,
    In Formula 1, R 8 is a heterocyclic compound of any one of Formulas 5a to 5o:
    Figure pat00051

    Figure pat00052

    In Formulas 5a to 5o,
    Z 1 , Z 2 , Ar 12 and Ar 13 are each independently a hydrogen atom, deuterium, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, a substituted or unsubstituted carbon group having 3 to 20 carbon atoms Heteroaryl group, a substituted or unsubstituted condensed polycyclic group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group or a carboxy group;
    p is an integer from 1 to 6;
    * Represents a bond.
  8. The method of claim 1,
    Heterocyclic compound wherein the compound of Formula 1 is any one of the following compounds:
    Figure pat00053
  9. A first electrode;
    A second electrode; And
    An organic layer interposed between the first electrode and the second electrode,
    The organic light emitting device of claim 1, wherein the organic layer comprises a first layer including the heterocyclic compound of any one of claims 1 to 8.
  10. The method of claim 9,
    The organic light emitting device is a functional layer having a hole injection layer, a hole transport layer, a hole injection and a hole transport function, a light emitting layer, an electron injection layer, an electron transport layer, or a functional layer having an electron injection and electron transport function at the same time. .
  11. The method of claim 9,
    The first layer is a hole injection layer, a hole transport layer, a functional layer having a hole injection and a hole transport function at the same time, a light emitting layer, an electron injection layer, an electron transport layer, or a functional layer having an electron injection and an electron transport function at the same time, the first An organic light emitting device in which the layer further comprises a charge-generating material.
  12. The method of claim 9,
    The organic light emitting device further comprises a functional layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination of two or more of which the organic layer simultaneously has a hole injection layer, a hole transport layer, a hole injection layer and a hole transport function.
  13. 13. The method of claim 12,
    And at least one of the hole injection layer, the hole transport layer, or a functional layer having both the hole injection function and the hole transport function further comprises a charge-generating material.
  14. 13. The method of claim 12,
    The light emitting layer includes a host and a dopant, and the dopant is a fluorescent dopant or a phosphorescent dopant.
  15. 15. The method of claim 14,
    The organic light emitting device wherein the phosphorescent dopant is an organometallic complex including Ir, Pt, Os, Re, Ti, Zr, Hf, or a combination of two or more thereof.
  16. 13. The method of claim 12,
    And the electron transport layer comprises an electron transport organic material and a metal-containing material.
  17. 17. The method of claim 16,
    Wherein the metal-containing material comprises a Li complex.
  18. The method of claim 9,
    An organic light emitting device in which the first layer is formed by a wet process using the heterocyclic compound according to any one of claims 1 to 8.
  19. The organic light-emitting device of claim 9,
    And a first electrode of the organic light emitting element is electrically connected to a source electrode or a drain electrode of the thin film transistor.
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Cited By (1)

* Cited by examiner, † Cited by third party
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US10069083B2 (en) 2014-06-02 2018-09-04 Samsung Display Co., Ltd. Condensed cyclic compounds and organic light-emitting devices including the same

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6329937B2 (en) * 2013-02-22 2018-05-23 保土谷化学工業株式会社 Organic electroluminescence device
KR101558495B1 (en) * 2014-06-27 2015-10-12 희성소재 (주) Polycyclic compound and organic light emitting device using the same
CN105646458A (en) * 2014-11-13 2016-06-08 上海和辉光电有限公司 Compound and preparation method and application thereof
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Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3816969B2 (en) 1994-04-26 2006-08-30 Tdk株式会社 Organic el element
DE69511755T2 (en) 1994-04-26 2000-01-13 Tdk Corp Phenylanthracene derivative and organic EL element
US5645948A (en) 1996-08-20 1997-07-08 Eastman Kodak Company Blue organic electroluminescent devices
US5972247A (en) 1998-03-20 1999-10-26 Eastman Kodak Company Organic electroluminescent elements for stable blue electroluminescent devices
JP2000003782A (en) 1998-06-12 2000-01-07 Casio Comput Co Ltd Electroluminescent element
EP1009043A3 (en) 1998-12-09 2002-07-03 Eastman Kodak Company Electroluminescent device with polyphenyl hydrocarbon hole transport layer
US6465115B2 (en) 1998-12-09 2002-10-15 Eastman Kodak Company Electroluminescent device with anthracene derivatives hole transport layer
DE10361385B4 (en) 2003-12-29 2011-07-28 OSRAM Opto Semiconductors GmbH, 93055 Polymers, phosphorescent, organic semiconducting emitter materials based perarylierter boranes, processes for their preparation and uses thereof
KR100700432B1 (en) 2005-01-13 2007-03-27 네오뷰코오롱 주식회사 Blue light-emitting oranic compound and organic light-emitting diode including the same
JP5048523B2 (en) 2005-02-23 2012-10-17 コーニンクレッカ フィリップス エレクトロニクス エヌ ヴィ Electroluminescent device containing iridium complex
JP4972938B2 (en) * 2006-01-12 2012-07-11 コニカミノルタホールディングス株式会社 Organic electroluminescent element material, organic electroluminescent element, display device and lighting device
JP2007186461A (en) 2006-01-13 2007-07-26 Idemitsu Kosan Co Ltd Aromatic amine derivative and organic electroluminescent element using the same
KR101528241B1 (en) 2007-12-07 2015-06-15 삼성디스플레이 주식회사 An Aromatic heterocyclic compound, an organic light emitting diode comprising an organic layer comprising the same and an method for preparing the organic light emitting diode
JP2010111635A (en) * 2008-11-07 2010-05-20 Canon Inc New azaindenochrysene derivative and organic light-emitting element
JP2012517422A (en) * 2009-02-06 2012-08-02 ソルヴェイ(ソシエテ アノニム) Phosphorescent luminescent iridium complexes containing pyridyltriazole ligands
TWI541234B (en) * 2009-05-12 2016-07-11 Universal Display Corp 2- organic light emitting diode of aza-linked material for the triphenylene
KR101182438B1 (en) * 2009-08-14 2012-09-12 삼성디스플레이 주식회사 Organic light emitting device
DE102009041414A1 (en) * 2009-09-16 2011-03-17 Merck Patent Gmbh metal complexes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10069083B2 (en) 2014-06-02 2018-09-04 Samsung Display Co., Ltd. Condensed cyclic compounds and organic light-emitting devices including the same

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